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  • 1
    Electronic Resource
    Electronic Resource
    Heterocyclen durch Anellierung an 4-Pyridinole, II Thieno[3,2-c]pyridin-3-ole (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 387-391 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocycles by Annelation to 4-Pyridinols, II.  -  Thieno[3,2-c]pyridin-3-olsHerrn Prof. Dr. Werner Schultheis zum 75. Geburtstag gewidmet.Thieno[3,2-c]pyridin-3-ols 4 are accessible from 4-hydroxy-3-pyridine carboxylates 1 via their 4-chloro derivatives 2 on replacement of the chlorine by mercaptoacetic esters and simultaneous ring-closure. Thioacetamide transforms the 4-chloropyridines 2 into 4-pyridinethiols 3, which likewise yield thieno[3,2-c]pyridin-3-ols 4 on reaction with chloroacetonitrile. The alkali salts of 4 are transformed into enol esters 5 by reaction with acid chlorides.
    Notes: Thieno[3,2-c]pyridin-3-ole 4 werden aus 4-Hydroxy-3-pyridincarbonsäureestern 1 über deren 4-Chlorderivate 2 und Austausch des Chlors mit Mercaptoessigsäureester bei gleichzeitigem Ringschluß erhalten. Thioacetamid überführt die 4-Chlorpyridine 2 in 4-Pyridinthiole 3, die mit Chloracetonitril ebenfalls Thieno[3,2-c]pyridin-3-ole 4 liefern. Die Alkalisalze von 4 werden mit Säurechloriden in Enolester 5 übergeführt.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790310
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  • 2
    Electronic Resource
    Electronic Resource
    Heterocyclen durch Anellierung an 4-Pyridinole, I Furo[3,2-c]pyridin-3-ole und Furo[3,2-c]pyridin-3(2H)-one (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 371-386 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocycles by Annelation to 4-Pyridinols, I.  -  Furo[3,2-c]pyridin-3-ols and Furo[3,2-c]pyridin-3(2H)-onesHerrn Prof. Werner Schultheis zum 75. Geburtstag gewidmet.The synthesis of furo[3,2-c]pyridin-3-ols 3 from 4-hydroxypyridinecarboxylates 2 is described. Hydrolysis of the ester group at C-2 of compound 3e yields furo[3,2-c]pyridin-3(2H)-one 4b (R4 = H) with loss of carbon dioxide. Condensation of 4b with aldehyds affords the unsaturated ketones 5, which on hydrogenolysis from furo[3,2-c]pyridin-3(2H)-ones 4 with an alkyl substituent at C-2. Alternatively compounds 4 are accessible on ring closure of 3-acyl-4-hydroxypyridines by bromination/dehydrobromination. The furo[3,2-c]pyridin-3-ols 3 and furo[3,2-c]pyridin-3(2H)-ones 4 are transformed into enol esters 15.
    Notes: Es wird die Synthese von Furo[3,2-c]pyridin-3-olen 3 aus 4-Hydroxy-3-pyridincarbonsäureestern 2 beschrieben. Hydrolyse der Estergruppe an C-2 von 3e führt unter Decarboxylierung zum Furo[3,2-c]pyridin-3(2H)-on 4b (R4 = H), aus dem mit Aldehyden die ungesättigten Ketone 5 erhalten werden, deren Hydrierung Furo[3,2-c]pyridin-3(2H)-one 4 mit Alkylresten an C-2 ergibt. Ein alternativer Zugang zu den Verbindungen 4 besteht im Ringschluß von 3-Acyl-4-hydroxy-pyridinen 14 durch Bromierung/Dehydrobromierung. Die Furo[3,2-c]pyridin-3-ole 3 und Furo[3,2-c]pyridin-3(2H)-one 4 werden in die Enolester 15 übergeführt.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790309
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  • 3
    Electronic Resource
    Electronic Resource
    Einfache Synthese von 4-(Heteroarylmethyl)phenolen und deren AcylierungHerrn Prof. Dr. Rolf Sammet zum 60. Geburtstag gewidmet. (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1392-1401 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Simple Synthesis of 4-(Heteroarylmethyl)phenols and Their AcylationCondensation of 4-hydroxybenzaldehyde (1) with ethyl acetoacetate (2a) or acetylacetone (2b) gives 3a and 3b, respectively, which on hydrogenation afford the 2-(4-hydroxybenzyl)-1,3-dicarbonyl compounds 4a and 4b, respectively. These react with hydrazines or hydroxylamine to give the 4-(4-pyrazolylmethyl)phenols 5 and the 4-(4-isoxazolylmethyl)phenol 6, respectively. Reaction of 4a with acetamidine affords 5-(4-hydroxybenzyl)-2,6-dimethyl-4-pyrimidinol (7a). On acylation with methyl isocyanate, 5a and 7a are esterified at the phenolic hydroxy group, whereas acyl chlorides react at the pyrazole OH group. In the case of 4-(3,5-dimethyl-4-pyrazolyl-methyl)phenol (5a) priority of O- or N-acylation depends on the base used.
    Notes: 4-Hydroxybenzaldehyd (1) wird mit Acetessigester (2a) oder Acetylaceton (2b) zu 3a bzw. 3b kondensiert, die zu den 2-(4-Hydroxybenzyl)-1,3-dicarbonylverbindungen 4a bzw. 4b hydriert werden. Diese liefern mit Hydrazinen oder Hydroxylamin die 4-(4-Pyazolylmethyl)phenole 5 bzw. das 4-(4-Isoxazolylmethyl)phenol 6. Aus 4a und Acetamidin wird 5-(4-Hydroxybenzyl)-2,6-dimethyl-4-pyrimidinol (7a) erhalten. Bei der Acylierung mit Methylisocyanat reagieren 5 sowie 7a unter Veresterung der phenolischen Hydroxygruppe. Säurechloride verestern dagegen die Pyrazol-OH-Gruppe. Beim 4-(3,5-Dimethyl-4-pyrazolylmethyl)phenol (5a) hängt der Vorrang von O- oder N-Acylierung von der eingesetzten Base ab.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800907
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  • 4
    Electronic Resource
    Electronic Resource
    Heterocyclen durch Anellierung an 4-Pyridinole, III. 2-Aminopyrido[3,4-e][1,3]thiazin-4-oneHerrn Prof. Dr. Rolf Sammet zum 60. Geburtstag gewidmet. (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1402-1408 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Heterocycles by Annelation to 4-Pyridinols, III1)  -  2-Aminopyrido[3,4-e][1,3]thiazin-4-onesHerrn Prof. Dr. Rolf Sammet zum 60. Geburtstag gewidmet.2-Aminopyrido[3,4-e][1,3]thiazin-4-ones 4 are obtained from 4-hydroxy-3-pyridinecarboxylic esters 1 via 4-chloro-3-pyridinecarboxylic esters 2 and reaction of the latter ones with thiourea. The 1,3-thiazin-4-one ring in 4 is very easily cleaved by alkali to give acylureas 5. Carboxylic chlorides and isocyanates react with compounds 4 at the thiazinone ring nitrogen to yield 3-acylpyrido[3,4-e]thiazinones 7, the structure of which is deduced from mass spectra. On the other hand chloroformic acid derivatives in N,N-dimethylformamide attack the exocyclic nitrogen to transform 4a into the dimethylformamidine 9.
    Notes: 2-Aminopyrido[3,4-e][1,3]thiazin-4-one 4 werden aus 4-Hydroxy-3-pyridincarbonsäureestern 1 über 4-Chlor-3-pyridincarbonsäureester 2 mit Thioharnstoff erhalten. 1,3-Thiazin-4-one 4 werden durch Alkali sehr leicht zu Acylharnstoffen 5 gespalten. Mit Carbonsäurechloriden und mit Isocyanaten reagieren die Verbindungen 4 am Thiazinonring-Stickstoff zu 3-Acylpyrido[3,4-e]-thiazinonen 7, deren Struktur aus den Massenspektren abgeleitet wird. Chlorameisensäurederivate in N,N-Dimethylformamid überführen dagegen 4a unter Angriff auf den exocyclischen Stickstoff in das Dimethylformamidin 9.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800908
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